21 Things to do in Chicago in the Winter (And What to Wear When It’s Freezing!)

Because it’s that time of the year again, and the “I’m visiting Chicago soon! Help!” DM’s have started rolling in on Instagram 😂I wanted to refresh this post that I wrote last year, tackling the topic of: “What the heck can I do in Chicago when it’s freezing?!”

I get this from visitors and locals alike. The good news is that no matter what the weather, there is always PLENTY to do in Chicago! I actually got a lot of these recommendations from you guys back when I asked what kinds of things to do with my mom when she came into town for Thanksgiving! (That and, of course, I threw in quite a few of my favorites as well!)

Another related question that I’m typically asked, is what to WEAR in Chicago in the winter. I’m sharing some of my favorite tips at the bottom of the post!

So, let’s jump in, shall we? Here are several things to do in Chicago in the winter, along with their google maps links so you can star your favorites! 😉

Winter Activities in Chicago:

Okay, this is kind of insane, but I’ve never actually been to RH. I know, it’s crazy. It’s become SUCH a staple here in Chicago and I’ve never met a person who didn’t go gaga for it. You’re probably saying, “Wait, like, the furniture store?” Yes, it IS a furniture store, but it’s so much more. Just watch this video. It’s essentially a gorgeous restaurant and cafe, with a garden, terrace–every inch of it asking to be instagrammed. This is definitely on my list to take my mom!

Afternoon Tea

Soho House (Their restaurant is called The Allis), The Drake, and the Peninsula all have very popular afternoon tea options. A great activity that doesn’t revolve around drinking, as so many other things in Chicago do, haha!

See a Play, Musical or Comedy Show

Chicago has SO many options to see plays and musicals! There is always an amazing broadway musical at the Cadillac Theatre, and Steppanwolfe always has an interesting play running! Chicago is also famous for its comedy scene and there are SO many options when it comes to comedy shows–Second City is a must, which is also a comedy school that churns out the top talent in the country, but there are so many great comedy clubs (here is a google maps listing so you can star away!)

Take in the view at one of Chicago’s Rooftop Bars and Restaurants

Chicago has so many rooftop bars–many of which are still a great spot to check out when it’s cold! There’s Cindy’s Rooftop, which is the rooftop restaurant at the Chicago Athletic Association hotel. Go for a drink before or after you check out the Bean and Millennium park. I also love The Robey’s rooftop, the Up Room (get there early to watch the sunset, it gets packed even on weekdays!) Both of these offer a view of the skyline you won’t see anywhere else! It’s also one of my favorite spots for brunch or coffee!

Neighborhood shopping

Whether you’re entertaining visitors or you’re the one visiting Chicago, make sure to get out of downtown, too! Tourist attractions are nice, but you’ll really fall in love with where the locals live. My two favorite shopping areas are in Wicker Park/Bucktown (a Western neighborhood–where I live!) and Lincoln Park (an Eastern neighborhood, by the lake!)

I know, technically this involves going OUTSIDE when it’s freezing in the winter months, but the shops in the following two neighborhoods (my faves) are super close together so you won’t have to be in the elements for too long before warming up!

In Lincoln Park, make sure to shop all along Armitage avenue (near the brown line Armitage stop!) and from there you can walk to Halsted street (go left on Halsted!)–both streets are lined with charming shops. When you get to the end of Halsted, take a stroll through Oz Park if the weather is nice enough!

Both of these neighborhoods also hold some of the best Chicago restaurants, so it’s easy to make a day out of exploring them! (Plus, they’re a quick Uber or bus ride from one to the other).

See a Chicago Blackhawks or Chicago Bulls game

I’m not the biggest sports fan in the world, but I love going to games at the United Center, where the Hawks and Bulls play! Truth: I go for the hot dogs. Who can blame me? Your husband will love it though 😜 Also, a plus: Hockey and Basketball are way easier to follow and more entertaining to watch than football 😉

The UC is also really close to the West Loop, which is known as “restaurant row” (a lot of Chicago’s hottest restaurants are in this neighborhood–two of our West Loop favorites are Girl and the Goat and BLVD).

Eataly is basically my Disneyland. I’ve never met anyone who hated Eataly! What’s not to love? All foodies will go googly eyed over all of the fine Italian goods. If you’ve never heard of it, it’s basically a gigantic beautiful gourmet store full of the finest Italian goods you’ve ever seen, combined with a few different gourmet Italian restaurants and bars ALL IN ONE. They have one main restaurant they flip every season–right now, it’s called BAITA, and it’s Italian Alps themed. You’ve never seen anything cuter or cozier! Go, go go! You can also take lot’s of different classes, from wine tasting to Gnocchi making!

I can’t tell you how many recommendations saying this was a go-to place to bring visitors from out of town. It’s swanky, posh, and delicious. Plus, it’s right on Michigan Ave, so it’s really convenient for shopping!

Chicago’s Famous Museums

The Field Museum, Museum of Science and Industry, Shedd Aquarium and Art Institute are world famous for good reason! I absolutely adore the Art Institute (make sure to grab lunch in their restaurant, it’s beautiful and overlooks the park!) I love their impressionist room. So many beauties by Monet!

This is around Christmastime but putting it in here if you happen to stumble upon it next year. I would usually tell most people to avoid Navy Pier like the plague but this actually looks like a cool family fun activity!

The same hotel that houses one of my favorite rooftop restaurants! The Game Room is one of the few “game” spots in the city that both serve alcohol AND allow kids during the day. And no, by “games” I don’t mean arcade or video games (thankfully). It’s a super swanky cocktail lounge that has billiards, bocce, shuffleboard, foosball, chess and checkers tables, and more. It’s also open until 3am on weekends! Whether you’re on a date or with your kids, this is a spot everyone will think is awesome.

Another gem from Mitch and Kelly. This is a bookstore that doubles as a bar/cafe–they have fun board games, too! They have a “laptop free” rule that encourages everyone to be offline and in the moment, which is a nice breath of fresh air!

This Wicker Park bar has TONS of beer on tap–32 beer, 8 wine taps, 4 Kombucha taps, 4 craft soda taps and 2 cold brew taps–to be exact. You also pour them yourself, so that’s part of the fun! They have board games you can drag out and play!

Again, I had never heard of this one either! (You guys really do give me the best ideas!) Did you know that Chicago’s suburb of Oak Park boasts more FLW homes than anywhere else in the world? The FLW trust organization offers a 3 hour tour, which is apparently phenomenal.

How to dress in Chicago Winter:

Okay, so we’ve covered what things to do in Chicago in the winter…but what do you wear? This is a very common question I get from visitors AND locals. How do you dress cute when it’s so darn cold?! 😭

Here are a couple quick tips:

Lot’s of layers:

The thing about Chicago is that it’s deathly cold outside, but when you get inside, you’re sweating. The key to navigating this temperature rollercoaster is to dress in layers–with a thin layer on the bottom, which seems counter-intuitive, but stick with me.

Base layers:

First, if I know I’m going to be out and about all day, I usually gravitate toward J.Crew’s tissue turtlenecks. I own them in lot’s of colors and they are my #1 winter staple. These are great because they add warmth but they look really adorable on their own, so when you strip off all your other layers, you still look put together.

I’ve also heard AMAZING things about Uniqulo’s Heat Tech items that are really thin and perfect for layering, but keep you super warm. I have yet to try these myself (it hasn’t been that cold yet) but I’m going to order some and will let you know! I’ll probably a tank version to wear as my first layer!

Another great option for your “bottom” layer on top is a button-down–my favorite are J.Crew’s chambray button-downs, because they look really cute under sweaters!

Top layers:

Second, layer a crewneck (I love Everlanes sweaters!) or cardigan sweater over the top. If you’d rather go with a turtleneck top layer, that’s cool too–but you may want to go with a tee or something under just for an additional layer (just make sure it’s something decent so you can remove your sweater if you’re too hot inside!) I love this chunky Everlane turtleneck and I’ve been living in it lately!

Bottoms:

Third, pair with dark pants or jeans, because they look dressier for dinner and you won’t feel the need to change! Whenever I’m out and about (especially in a new city I’m visiting) I don’t like having to go back to the hotel to change for dinner, so dark jeans are a great thing to wear since they transition so well from day to night.

When it’s cold, I usually opt for skinny jeans, since they’re the best for wearing with boots. Abercrombie’s skinnies and Everlane authentic stretch skinnies) are the two pairs I wear most often, and I also really love Spanx Velvet leggings because they’re super warm (warmer than normal leggings because they’re much thicker) but incredibly comfortable! If you’re someone who gets REALLY cold you could also layer some heattech tights underneath!

Do you need long underwear?

Do you need long underwear in the winter in Chicago? Personally, I would say no unless you’re planning an all-day wilderness hike. Kelly would say 100% yes and she wears long underwear daily. Use your best judgement! 😂

(Again, heattech under layers might be worth looking into–but I guess I get warm enough with my warm coat while walking, and then I get too hot inside if I have TOO many layers on, so it’s really a personal decision!)

Do you REALLY need a Canada Goose coat?

You most definitely need a VERY warm coat–my life changed when I got a Canada Goose coat. (Previously I’d worn a North Face coat, which is warm, but not AS warm–no matter how cold it is outside I don’t shiver when I’m wearing it–which says A LOT.)

Here’s the thing though: Canada Goose parkas are VERY expensive. It’s honestly ridiculous (and no, I don’t like that it has real fur–I wish they made an option without it) but it lasts forever and I’ve never met ONE person who was like, “Oh, I wish I hadn’t bought that Canada Goose–it’s not worth the money.” Seriously. Said no one EVER.

The GREAT news though, is that I recently got Lole’s Marybeth parka (I’m doing a collab with them and they graciously agreed to send me a few coats to compare/review for you guys, because I know you’re always looking for more affordable Canada Goose alternatives! NOTE: I don’t have photos of it yet though, above is my Canada Goose) and it is VERY, VERY warm. It is as warm as Canada Goose–and is 700 fill power (the warmth measurement they use for down coats) which is actually WARMER than a Canada Goose! (Canada Goose is 650 fill power).

However, the differences are in the details–these are very minor things but can be important based on your lifestyle:

The Marybeth coat is not AS form-fitting as Canada Goose, which has a very feminine shape. It’s still not “puffy” which I love, but if shape is the biggest factor to you after warmth, it’s just something to note.

Very nit-picky, but the pockets on the Marybeth coat aren’t as deep or as angled, so your hands don’t stay as warm AND I always fear my phone is going to fall out of them. When you zip it up all the way, there is more room in the neck of the Marybeth than on the Canada Goose, which is super snug at the neck–so it doesn’t let as much cold air in.

Additionally, the Canada Goose has straps inside that you loop your arms through that allow you to take your coat off and still have it strapped to you–almost like you’re wearing it as a backpack–(i.e. while standing in line to get coffee, riding the subway, etc–places you are DYING to take off your coat because it’s so stifling inside but can’t because it’s too much work to get it back on or you have your hands full).

BUT–those are very reasonable negotiables and may not justify several hundred more dollars for you. If budget is your main factor, I don’t think these nit-picks are going to be worth the $500 price difference–I definitely think the Marybeth is an excellent route to go! On the flip side, if you do have the funds, and the above details are important to you, you are never going to be sorry you got the Canada Goose. There is no wrong choice here!

Another fantastic, and less-expensive option, is Lole’s Katie coat–which I would say is a warmth equivalent to a North Face puffer–but SOOO much cuter! I actually have been wearing my Katie coat the most lately (again, it’s still November, so the bone-chilling cold that is Chicago in February has not hit yet). I think the Katie coat is by far the cutest puffer I’ve ever seen–and it’s really hard to beat the price. I’d definitely opt for it over a Northface or Patagonia.

A nice pair of jeans and flat boots are acceptable just about everywhere:

Another question I get a lot–what do you wear out? The best part about Chicago is that nobody is ever going to turn you away for wearing jeans and flat boots, even in a super nice restaurant. Things are just more casual here. On the flip side, if you want to get dressed up and wear a dress and heels, nobody will look at you funny! (The Midwest is nice like that.) But as a general rule, don’t feel like you have to wear heels anywhere.

Quick tip: The taller your boots are, the warmer you will be. This is never something I realized until I got a pair of OTK boots and realized they add the warmth equivalent of about three pairs of pants, so if you have them, definitely wear them as often as possible. BUT. Please, please, for me, and yourself–make sure you spray them with LOTS of suede protectant beforehand! (It doesn’t matter what kind, just SOMETHING.)

My favorite pairs are the Stuart Weitzman Lowlands (splurge) but Blondo’s OTK boots are the budget-friendly pair I recommend to EVERYONE. They are actually fully waterproof, so no suede protectant necessary–and they are so beautiful and no break-in is required!

Hats, scarves, and gloves really make a difference:

They go a LONG way in keeping you warm–and make sure they match the rest of your outfit, too, or else you’ll feel like a 5 year old getting ready to go out on the playground 😂 I speak from experience. Seriously, buying a couple different neutral colors will get you a long way and make you love your outfit SO much more!

Shop hats, scarves, and gloves:

What are YOUR favorite things to do in Chicago in the winter? Any layering tips that have worked especially well for you? Would love to hear them!

I live in FL so I have 0 knowledge on how to layer for super cold weather ha (never even seen snow)! If I ever were to go to a snowy place, I’d come to this blog! Seriously, I’ve been to so many other blogs and they tell you how to look cute but it never seems truly applicable on dressing for superrrrr cold winters.

Funny story, I went to Dillard’s yesterday to shop shoes and I found the perfect OTK light grey boot for only $60. When I tried them on I noticed how warm they actually were. The great thing about that though is that even when it cools down here (it’s gotten in the low 30’s this winter!) I can still pull them off with a skirt and not sweat to death. But I have not worn them yet. Next week will be the true test to tell if they are warm-er winter weather approved.

Last year was my first Chicago winter and I really just tried to survive. This year I’m trying to mesh my style with the elements and it’s proving way more difficult than I imagined. I really appreciate these tips and the recommendations on things to do in the city!

Bit late to this post but the best tip I have is fleece-lined tights! You can wear them under pants or leggings if it’s REALLY cold (like sub-zero) and if it’s normal cold you can still wear cute dresses and skirts all winter.

I am so glad you shared this post- I’m headed to West Chester PA tomorrow and the high is only 35! For a Florida girl this is freezing! And I’m working while I’m there so being business casual is important too. Super helpful!!

They also just opened another tapster in Lincoln park! On Wrightwood and Seminary, kinda nearby the Broken English over there. They only opened about a month or two ago and my friends and I have already been like 4 times! lol! Not as many taps as the Wicker location but they still have a good amount (prob 25/30 total?) and still include cider/’buch/cocktails etc.

If you hate layering bottoms (tights under jeans so your legs don’t fall off from the cold), Old Navy has some of their Rockstar skinnies with a build in warming layer. They are seriously life changing and I’m about to go back to buy more!

Love all those fun things you listed! I still haven’t been to Eataly and need to go!! I almost convinced my friends the last time we were in Chicago but they had other things they wanted to do…. so next time it will be a non-negotiable!!

Great post! I moved to Chicago from Alabama last year and one thing I have developed is a love for Cashmere. I would never be able to wear it in the South, but I love it now. So soft and warm. Also, my mother just bought me a pair of Blondo boots and I’ve been wearing them this week through the snow. I love them because they are warm and waterproof, but nice enough I don’t have to change shoes when I get to work. Still debating on the Canada Goose.